HCID 58123948, compound → HCID 54557496, compound

HRID 1616663Notes

Reaction equation

HRID 1616663 reaction equation
C([N:8]1[CH2:15][CH2:14][C@:13]2([CH3:19])[C:16]([CH3:18])([CH3:17])[C@H:9]1[CH2:10][C:11]1[C:23](OS(C(F)(F)F)(=O)=O)=[CH:22][CH:21]=[CH:20][C:12]=12)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:19][C@:13]12[C:16]([CH3:17])([CH3:18])[C@H:9]([NH:8][CH2:15][CH2:14]1)[CH2:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]2=1

Participants

4

Reactant 1

HCID 58123948HCID 58123948, compound

Product 1

HCID 54557496HCID 54557496, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (0.20 g) is added to a solution of (2R,6S)-trifluoro-methanesulfonic acid 3-benzyl-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-yl ester (0.50 g) in ethanol (10 mL). The resulting mixture is shaken under hydrogen atmosphere (50 psi) at room temperature overnight. Then, the catalyst is separated by filtration and Pd(OH)2 (0.2 g) is added to the filtrate (the benzyl group was not completely removed after the treatment in the presence of Pd/C). The mixture is shaken in hydrogen atmosphere (50 psi) at room temperature for another 16 h. The catalyst is separated and the filtrate is concentrated under reduced pressure to give the crude product that is used without further purification.

Workup

  1. customThen, the catalyst is separated by filtration and Pd(OH)2 (0.2 g)
  2. additionis added to the filtrate (the benzyl group
  3. customwas not completely removed after the treatment in the presence of Pd/C)
  4. stirringThe mixture is shaken in hydrogen atmosphere (50 psi) at room temperature for another 16 h
  5. customThe catalyst is separated
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-771a268179bd4018b9bd5f2839eb6dca
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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